(R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester

Base Information

• Chemical Name: (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester
• CAS No.: 137445-70-6
• Molecular Formula: C₂₉H₃₉NO₈
• Molecular Weight: 529.631
• Mol file: 137445-70-6.mol

Synonyms:

Chemical Property of (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester

There total 19 articles about (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester (137445-70-6)

Guidance literature:

Multi-step reaction with 19 steps

1: 99 percent

2: 72 percent / PCC, 3 Angstroem mol. sieves, Celite / CH₂Cl₂ / 25 °C

3: 93 percent / PPTS / benzene / Heating

4: (S)-BINAL-H / tetrahydrofuran / -100 - -78 °C

5: 100 percent / Bu₄NF / tetrahydrofuran / 25 °C

6: 97 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 0 - 25 °C

7: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

8: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

9: 1) LDA, 2) HMPA, t-BuMe₂SiCl / 1) THF, -78 deg C, 2) -78 deg C - 25 deg C

10: diethyl ether / 25 °C

11: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

12: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) CH₂Cl₂, -60 deg C, 2) 60 deg C to 25 deg C

13: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

14: TiCl₄ / CH₂Cl₂ / -78 °C

15: 95 percent / Bu₄NF / tetrahydrofuran / 25 °C

16: 97 percent / Na/NH₃ / tetrahydrofuran / -78 °C

17: 97 percent / DMAP, DCC / CH₂Cl₂

18: 81 percent / KOH / methanol

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; oxalyl dichloride; (-)-(S)-BINAL-H; 3 A molecular sieve; Celite; tetrabutyl ammonium fluoride; ammonia; sodium; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92272-X

Reference yield:

(S)-7-(5,9-Dihydro-6,8-dioxa-benzocyclohepten-7-yl)-hept-2-yne-1,4-diol → (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester (137445-70-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 97 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 0 - 25 °C

2: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

3: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

4: 1) LDA, 2) HMPA, t-BuMe₂SiCl / 1) THF, -78 deg C, 2) -78 deg C - 25 deg C

5: diethyl ether / 25 °C

6: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

7: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) CH₂Cl₂, -60 deg C, 2) 60 deg C to 25 deg C

8: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

9: TiCl₄ / CH₂Cl₂ / -78 °C

10: 95 percent / Bu₄NF / tetrahydrofuran / 25 °C

11: 97 percent / Na/NH₃ / tetrahydrofuran / -78 °C

12: 97 percent / DMAP, DCC / CH₂Cl₂

13: 81 percent / KOH / methanol

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonia; sodium; titanium tetrachloride; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92272-X

Reference yield:

(E)-(S)-7-(5,9-Dihydro-6,8-dioxa-benzocyclohepten-7-yl)-hept-2-ene-1,4-diol → (R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester (137445-70-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

2: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

3: 1) LDA, 2) HMPA, t-BuMe₂SiCl / 1) THF, -78 deg C, 2) -78 deg C - 25 deg C

4: diethyl ether / 25 °C

5: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

6: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) CH₂Cl₂, -60 deg C, 2) 60 deg C to 25 deg C

7: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

8: TiCl₄ / CH₂Cl₂ / -78 °C

9: 95 percent / Bu₄NF / tetrahydrofuran / 25 °C

10: 97 percent / Na/NH₃ / tetrahydrofuran / -78 °C

11: 97 percent / DMAP, DCC / CH₂Cl₂

12: 81 percent / KOH / methanol

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; potassium hydroxide; oxalyl dichloride; tetrabutyl ammonium fluoride; ammonia; sodium; titanium tetrachloride; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92272-X

upstream raw materials:

(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-hydroxymethyl-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(diethoxy-phosphoryl)-5-oxo-hexanoic acid 4-nitro-phenyl ester

3,4,5,6-tetrahydro-2H-pyran-2-one

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one

Downstream raw materials:

(+)-dihydrocompactin